2,6-dimethyl-4-(4'-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester | 77233-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-dimethyl-4-(4'-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester
• 英文别名: dimethyl 2,6-dimethyl-4-(4-nitrophenyl)pyridine-3,5-dicarboxylate；dimethyl 4-(4-nitrophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate；4-(4-nitrophenyl)-2,6-dimethyl-3,5-dimethoxycarbonyl-pyridine
• CAS: 77233-99-9
• 化学式: C₁₇H₁₆N₂O₆
• 分子量: 344.324
• InChiKey: DMKXWKHBAXUABP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  氨基硫脲 、 2,6-dimethyl-4-(4'-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester 在 吡啶 作用下， 以 乙醇 为溶剂， 以58%的产率得到2,2'-(2,6-dimethyl-4-(4-nitrophenyl)pyridine-3,5-dicarbonyl)bis(hydrazine-1-carbothioamide)
  参考文献：
  名称：

  Microwave Assisted Synthesis of Some Pyridine Derivatives Containing Mercaptotriazole and Thiazolidinone as a New Class of Antimicrobial Agents

  摘要：

  A fast and facile procedure for the synthesis of pyridomereaptotriazole 4a-e and pyridothiazolidinone 5a-e is being reported starting from diliydropyridine 1a-e. Subsequent oxidation with nitrating mixture (HNO3/H2SO4) produced the anticipated 2,6-dimethylpyridine derivatives 2a-e, which were subsequently condensed with thiosemicarbazide in ethanol to produce the key intermediate 2,2'-[4(4-substituted phenyl)- 2,6-dimethylpyridine-3,5-diyl]dicarbonyldihydrazine carbothioamides 3a-e. In the final step pyridomercaptotriazole derivatives 4a-e were synthesized by treating 3a-e in alkaline media. In parallel pyridothiazolidinone derivatives 5a-e were obtained by the reaction of 3a-e with ClCH2COOH/CH3COONa. All the reactions were carried out on microwave irradiation in good yield with short time. The structures of all the compounds have been confirmed on the basis of their analytical, IR, H-1 NMR, and Mass spectral data (Tables I and II). The potent antimicrobial effects of the synthesized compounds were also investigated.

  DOI：

  10.1080/10426500701557138
• 作为产物：
  描述：

  乙酰乙酸甲酯 在 manganese(IV) oxide 、 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.19h， 生成 2,6-dimethyl-4-(4'-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Microwave-Assisted Oxidative Aromatization of Hantzsch 1,4-Dihydro­pyridines using Manganese Dioxide

  摘要：

  4-芳基和4-烷基-1,4-二氢吡啶通过微波辅助的Hantzsch反应制备，在没有无机支持的情况下，使用商业锰氧化物在100°C的微波照射下，仅需一分钟即可高效芳香化。此快速程序比使用Pd/C、碘或邻碘代苯甲酸（IBX）的微波辅助芳香化更为高效，脱氢或4-去烷基的产物产率为91-100%（13个示例）。

  DOI：

  10.1055/s-2006-926407

文献信息

• A simple, efficient, one-pot three-component domino synthesis of Hantzsch pyridines under solvent-free condition
  作者：Masoud Nasr-Esfahani、Bahador Karami、Masoume Behzadi

  DOI：10.1002/jhet.175

  日期：2009.9

  In this article, efficient and simple preparation of Hantzsch pyridine derivatives by reaction of various aldehydes and β-dicarbonyls in the presence of ammonium chlorate under solvent-free condition at 80°C is reported. The advantages of this system are the one-step procedure, high yields of the products, and the ability to carry out large-scale reactions. J. Heterocyclic Chem., (2009).

  在本文中，通过在乙腈存在下各种醛与β-二羰基的反应，可以有效而简单地制备Hantzsch吡啶衍生物 据报道在80°C无溶剂条件下的氯酸铵。该系统的优势在于一步法，高收率的产品以及进行大规模反应的能力。J.杂环化​​学，（2009）。
• Reactivity of 1,4-Dihydropyridines toward Alkyl, Alkylperoxyl Radicals, and ABTS Radical Cation
  作者：C. López-Alarcón、P. Navarrete、C. Camargo、J. A. Squella、L. J. Núñez-Vergara

  DOI：10.1021/tx025579o

  日期：2003.2.1

  tested for potential scavenger effects toward alkyl, alkylperoxyl radicals, and ABTS radical cation in aqueous media at pH 7.4. Kinetic rate constants were assessed either by UV/vis spectroscopy or GC/MS techniques. Tested compounds reacted faster toward alkylperoxyl radicals and ABTS radical cation than alkyl ones. N-Ethyl-substituted DHPs showed the lowest reactivity. Kinetic results were compared with

  合成了一系列在二氢吡啶环中具有仲氮或叔氮的C4取代的1,4-二氢吡啶（DHP）。测试了所有这些化合物以及一些商业DHP衍生物在pH 7.4的水性介质中对烷基，烷基过氧自由基和ABTS自由基阳离子的潜在清除作用。动力学速率常数通过紫外/可见光谱或GC / MS技术进行评估。被测化合物对烷基过氧自由基和ABTS自由基阳离子的反应比烷基化合物更快。N-乙基取代的DHP显示最低的反应活性。动力学结果与trolox或尼索地平进行了比较。使用氘动力学同位素效应研究，我们证明了DHP环1位的氢参与了拟议的机理。在烷基的情况下，这一事实最为明显。在所有情况下，各自的吡啶衍生物被检测为反应的主要产物。
• Mannich reaction of dihydropyridine derivatives I. Reactions with secondary amines.
  作者：JIRO ARITOMI、SHOZO UEDA、HARUKI NISHIMURA

  DOI：10.1248/cpb.28.3163

  日期：——

  Dialkyl 4-aryl-1, 4-dihydro-2, 6-dimethylpyridine-3, 5-dicarboxylates (III) were subjected to the Mannich reaction with excess paraformaldehyde and secondary amine hydrochloride in boiling ethanolic solution. When the compounds III were treated with a 5-to 7-fold molar excess of the aldehyde and amine salt, 2, 6-bis (2-disubstituted aminoethyl)-dihydropyridine derivatives (V) were obtained in good yields. On treatment with a 2- to 3-fold molar excess of the reactants, compounds III were converted to 2-(2-disubstituted aminoethyl)-6-methyldihydropyridine derivatives (IV) and V. When dioxane was used as a solvent with a 6-fold molar excess of the reactants, the tetrakis (dimethylaminomethyl) derivative (VII) was obtained.

  二烷基 4-芳基-1, 4-二氢-2, 6-二甲基吡啶-3, 5-二羧酸酯 (III) 在沸腾的乙醇溶液中与过量的多聚甲醛和二级胺盐酸盐进行曼尼希反应。当化合物 III经5-至7-倍摩尔过量的醛和胺盐处理时，可获得产率良好的 2, 6-双(2-二取代氨基乙基)-二氢吡啶衍生物 (V)。用2-至3-倍摩尔过量的反应物处理时，化合物 III 转化成 2-(2-二取代氨基乙基)-6-甲基二氢吡啶衍生物 (IV) 和 V。当使用二氧六环作为溶剂并采用6-倍摩尔过量的反应物时，得到四(二甲氨基甲基)衍生物 (VII)。
• BIFC and QFC promoted rapid and cleaner aromatization of 1,4-dihydropyridines under solvent-free condition
  作者：Vajiravelu Sivamurugan、Velayutham Murugesan、Valiyaveettil Suresh、Muthaiyahpillai Palanichamy、Ajayan Vinu

  DOI：10.1002/jhet.5570440438

  日期：2007.7

  This communication expresses aromatisation of 1,4-dihydropyridines to pyridine derivatives with the help of alumina supported benzimidazolium fluorochromate (BIFC) and quinolinium fluorochromate (QFC) as oxidants under solvent-free microwave irradiation. Moderate to excellent yield (80-98%) of pyridine derivatives were achieved by this methodology.

  这种交流表示在无溶剂微波辐射下，借助于氧化铝负载的氟代苯并咪唑鎓铬酸盐（BIFC）和氟代喹啉鎓铬酸盐（QFC），可以将1,4-二氢吡啶芳构化为吡啶衍生物。通过这种方法，吡啶衍生物的产率中等至优异（80-98％）。
• An Efficient Transition-Metal-Chloride/Sodium-Nitrite/TEMPO Catalytic System for Aerobic Oxidative Aromatisation of Hantzsch 1,4-Dihydropyridines
  作者：Bin-Hui Lou、Shu-Bin Chen、Jian Wang、Ying Chen、Jing-Hua Li

  DOI：10.3184/174751913x13701832537930

  日期：2013.7

  A facile and efficient transition-metal-chloride/sodium-nitrite/TEMPO catalytic system for aerobic oxidative aromati-sation of Hantzsch 1,4-dihydropyridines in high yields under mild conditions is described.

  本文介绍了一种简便高效的过渡金属氯化物/亚硝酸钠/TEMPO 催化系统，该系统可在温和的条件下有氧氧化芳香化汉茨奇 1,4-二氢吡啶并获得高产率。